I’ve been focused on writing songs for fifteen years.

When I started this newsletter, I thought I was starting over.

Writing prose?

That felt like a separate craft to me.

A separate 10,000-hour mountain I’d have to climb.

I couldn't help but kick myself for wasting time.

Better start climbing…

And once I did, I was surprised how much the craft of writing songs helped.

Songwriting taught me to say more with less.

Sometimes you only get three or four words to state your whole idea.

You’re walking a musical tightrope.

Trying to fit words to melody.

You switch up the syntax, subtract all but the essential.

And somehow you make it sound like something you’d say out loud.

A paragraph has more room than a chorus, but the same principles apply.

Each extra word makes the reader work harder.

And if you can’t say it in plain English, you probably don’t know what you’re saying yet.

But I learned something more in the process. Something about myself.

I’m a writer first.

A writer who happens to speak music.

Because music is the most natural way for me to express myself.

I was the kid in school who loved writing essays. I’d lose myself in the process.

And I still do.

Whether it’s a chorus, a newsletter, or a half-baked attempt at a poem.

The process of writing carries over.

And I doubt that’s just a songwriter thing.

It reminds me of that saying, “how you do anything is how you do everything.”

Maybe it’s more like, “how you write anything is how you write everything.”

Which means none of that time was wasted.

Chances are the thing you’ve spent years getting good at is training you for your next mountain.

You won’t know until you start climbing.

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This is the 75th issue of Shaping Song.

For this one, I’m going back to an early piece that I consider one of my most valuable.

Most of you weren’t here when it first went out, so I wanted to share it one more time.

In a world where artists are expected to create nonstop, speed is a superpower.

When I started my songwriting journey it would take me weeks to finish one song.

Now I can write one between breakfast and lunch (and still have time for a pre-lunch workout).

I do this by embracing creative constraints.

Unfortunately, most writers waste years writing songs without ever setting constraints for themselves.

Why?

They don’t understand the power of limitation.

Creative constraints are boundaries you set for yourself.

They help you get more work done by giving you less to work with.

The greatest writers of all time did this.

Robert Frost likened writing free verse (poetry without a regular meter) to playing tennis without a net.

You might think this would crush your creative spark.

But constraints actually make you more creative.

Because when you limit your options, you’re forced to stretch yourself to come up with something unique. Something that fits within the guidelines you’ve set.

Not only that… you get to choose the constraints you work with.

You can even invent your own.

In this newsletter, I’d like to share three of the most helpful constraints I’ve found so you can use them to write more songs in less time.

Perfect Rhyme

Rhymes are considered “perfect” when they end with matching vowel and consonant sounds, like smash and crash.

“Imperfect” or “slant” rhymes have matching vowel sounds with different consonants at the end, like smash and craft.

Perfect rhyme helps you write fast by giving you fewer options to work with.

The one trick to using perfect rhyme:

Avoid clichés like a cat avoids a bath (which pretty much rules out the word love).

Are you starting to see how this can boost creativity?

Using perfect rhyme makes you stretch to find new and better words.

Try it for yourself:

Write your next song using 80% perfect rhyme.

Notice how the perfect rhyme feels in comparison to the imperfect rhyme.

Start With The Title

A mentor of mine told me:

“Starting a song without a title is like driving around town on an empty stomach looking for something to eat.”

Bad decisions at every turn.

When you start with a title, you know where you’re going.

Now all you have to do is let the lyrics lead you there.

You can even write backwards from the title. As Paul Simon says:

Whatever way you choose, this makes your songs more clear.

And when your songs are more clear, they have a better chance of connecting with your audience.

Writing more songs in less time AND building a better connection with your audience...

These constraints are starting to look pretty good.

Structure Each Section’s Melody Using AABA

This one took me years to learn.

We know about song form. But great songwriters go deeper.

They see the hidden structure inside every section.

The chorus melody has a structure. So does the verse melody.

The most efficient one I’ve found is AABA:

• Do something once

• Now repeat that thing

• Now do something different

• Now go back to the first thing one last time

This is a quick way to create a feeling of completion for the listener.

It also eliminates the question, “do we need a pre chorus?”

No, we don’t.

The song feels great just like this:

• Verse 1 - AABA

• Chorus 1 - AABA

• Verse 2 - AABA

• Chorus 2 - AABA

• Break (repeat the title and/or ad-lib melodies over the same chords).

• Chorus 3 - AABA

Assuming your chorus doesn’t change, this lets you write a 12 line song.

Now the only question is, how long does it take you to write 12 lines?

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Back when I worked at a music store, I overheard one of my coworkers talking with a customer who came in shopping for a guitar.

They bonded fast over one thing.

Neither of them could read music, and they were proud of it.

I heard them saying things like:

“Music theory kills your creativity.”

“Hendrix didn’t know how to read music.”

“Irving Berlin played using just the black keys!”

It almost made me feel stupid for having gone to music school.

But they were just insecure about their lack of knowledge.

And instead of going through the pain of learning, they told themselves they were better off because of it.

Learning music theory doesn’t somehow make you less “artistic.”

And calling ignorance a creative choice doesn’t make it one.

Don’t get me wrong, you don’t have to learn music theory.

The problem is deciding you’re done learning, and calling that artistry.

Jimi Hendrix couldn’t read music, but he never stopped learning what made his music work.

When I'm writing a song, I don’t think about music theory at all.

But knowing theory gives me more options in the rewrite.

It lets me add tension to a top line.

It helps me find the right wrong notes.

Knowing how music works only gives you more options for the chopping block.

But your heart decides which ones make the cut.

Producer and author Jesse Cannon makes a point in his book, Processing Creativity, that stuck in my head.

He says the most important skill in making music is trusting how you react to it.

As you listen back to your work in progress, you notice your gut reaction.

You follow that feeling, shaping your song until it matches what your heart wants to say.

You know it’s done when nothing jumps out at you anymore.

That’s what putting your heart first looks like.

Without theory, you still know something is off.

You just have fewer ways to fix it.

Those two guys at the music store thought they were protecting their creativity.

But they were only protecting their egos.

Knowledge doesn’t ruin your art.

Pretending you don’t need it might.

And you don’t need to take college level music theory or study counterpoint.

A basic understanding of how chords work together will do.

You can learn that on your own, by listening to music you already love.

Study the songs that wreck you until you have an intuitive feeling for why they work.

Then forget it all and just write something.

When you listen back, listen for what moves you and what doesn’t.

Learn to trust that.

That’s your heart.

It’s been learning the whole time.

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When it comes to writing lyrics, I do my best to be clear.

I like songs that make sense,

and I don’t take my craft lightly.

But sometimes I wonder if I take clarity too far…

I want my songs to be more artistic. More unhinged.

But when I sing an abstract line, it feels clunky coming out of my mouth.

Some singers can get away with anything.

Marcus Mumford could move millions singing, “The Muffin Man.”

Kristian Matsson, a.k.a. The Tallest Man on Earth, strings together images that make no literal sense. But his voice makes you believe every word.

I’m not that kind of singer.

So I’ve learned to lean on my lyrics.

A while back I wrote a whole newsletter about Stephen Sondheim.

His four principles for writing lyrics.

The one I loved most was the last one. Where he says that all other rules are in the service of clarity, “without which nothing else matters.”

I still believe that.

But clarity has a ceiling:

• A clear line is easy to understand.

• But a little madness gets under your skin.

The best songs have a balance of both.

And then there are people like Tom Waits. Beck. John Lennon…

Nobody ever accused any of them of having angelic voices.

But they found their own madness.

Listen to “Across The Universe.” The lyric reads like a science fiction fever dream. Still, you know exactly what he’s saying.

Same with Beck’s “Loser.”

Or take any Dylan Thomas poem. Read it out loud.

Your head can’t explain half of it.

But your heart gets every word.

So maybe it’s less about the voice and more about the conviction behind it.

No one hears you the way you hear yourself.

The line that feels vague to you might give someone else goosebumps.

There’s no way to predict how someone else is going to hear your song.

And for me, that’s hard to swallow.

Admitting I may not know what I’m trying to say at all.

Sitting with that uncertainty.

Committing first and letting the meaning reveal itself in time.

Because people will tell you what your song means to them.

And nine times out of ten, you’ll find their meaning to be better than anything you could have come up with on your own.

So that’s what I’m practicing.

Writing lines I can’t fully explain.

Words that just sound good and feel good on a gut level.

And singing them like I believe them.

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Most people say songwriting is instinct over intellect.

You’re supposed to feel your way through a song…

“Capture the ghost in the room.”

The second you think too much, your work gets stale.

I call BS.

Of course, there has to be that flicker of inspiration.

But that’s where the real writers know they’re just getting started.

I’ve always appreciated when a songwriter brings a certain level of intellect to their work.

People like Paul Simon, Joni Mitchell, Randy Newman…

They take music and song to a scholarly level.

This week I’m reading a book about decision-making and chaos theory.

How small choices compound into events you could never map out in advance.

I’ve also got a new song in the works…

The other day, as I was working on my lyric, a line popped into my head that reminded me of what I was reading.

Something like, “all the wrong roads led me right to you…”

How we can never judge what’s good or bad in the moment, because we never know where events will lead.

Chaos theory.

My search for the song brought me back to the book.

And going back to the book helped me finish my chorus.

A positive feedback loop.

Still, the book has nothing to do with love.

They say writing about what you learn helps you internalize it.

But what if that doesn’t mean just taking notes?

What if it could be a poem, a painting, or a song?

Nobody listening to my song is going to think about chaos theory.

If I do my job right, they won’t be thinking much at all.

The writing process is really just for me.

I get to do the thinking regardless of how the song turns out.

I turned the idea over in my mind. Simplified it enough to fit three minutes of melody.

That’s not a lesser form of thinking than writing an essay.

It may even be a harder one.

So can songwriting be an intellectual pursuit?

I think it can.

But not because the songs sound smart.

Most of mine try not to.

Songwriting becomes an intellectual pursuit when you take a big idea and dumb it down in the process.

Dumb it down until it’s simple enough to sing over four chords.

Bonus points if you can make it feel true.

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I spent six years in LA trying to fit my songs into a commercial box.

Dissecting the hits. Following formulas.

Pouring my best creative hours into trying to sound like everyone else.

It’s no wonder I almost completely burned out…

We’ve heard it before.

Comparison is the thief of joy.

But whose joy are we actually stealing?

Every minute you spend measuring your path against someone else’s is a minute you’re not walking your own.

That’s a minute of your gift the world will never get.

In that sense, comparison doesn’t just cost you.

It costs everyone who needs what only you can do.

There’s a story I love about Miles Davis.

When he decided to drop out of Juilliard and immerse himself in the jazz scene of New York City, he went home to tell his parents.

Miles shares his dad’s reaction in his autobiography:

“Okay,” he said, “as long as you know what you’re doing, everything is okay. Just whatever you do, do it good.”

Then he told me something I will never forget:

“Miles, you hear that bird outside the window? He’s a mockingbird. He don’t have a sound of his own. He copies everybody’s sound, and you don’t want to do that. You want to be your own man, have your own sound. That’s what it’s really about. So, don’t be nobody else but yourself.”

The moment I stopped chasing what everyone else was doing and started writing the songs I wanted to write, my work got better.

I felt better too.

Because I finally believed in my music again.

I finally believed it was worth the time, no matter the outcome.

I stopped comparing my work against others and went back to studying the all time greats.

The stuff that made me want to write songs in the first place.

Looking back, I don’t regret the years I spent writing songs to be more mainstream and commercial.

I learned a lot in that process.

And that learning bleeds into my work now.

But if I hadn’t stopped measuring my songs against what was working in the marketplace, I never would have fallen back in love with my craft.

I never would have gotten back to my own path.

Because at the end of the day, you can’t win music or art or poetry.

The best you can do is sing your own song.

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I was having lunch with an artist friend the other day.

We were talking about the similarities between art and music.

That’s when she said something that goes against my entire songwriting ethos:

“Songwriting is poetry…”

Now, I’ll admit, it’s a nice little ego boost whenever someone says this.

We all want to be poets.

But there’s a big difference between poetry and song.

A poem stands on its own. It has to sing without music.

A lyric gets to lean on a melody.

It can certainly be poetic.

But don’t confuse a poetic lyric with poetry.

A lyric can say exactly what it means in plain English.

No twist of phrase or figure of speech necessary.

A lyric can also be so musical that it sings on its own as if it were poem.

(See Paul Simon, Joni Mitchell, Leonard Cohen…)

But saying that all lyrics are poetry is a trap we must avoid as songwriters.

Not only will it cramp our creativity, it will get in the way of the one thing that matters most of all:

Clarity.

Saying exactly what you mean.

It sounds like such a simple thing to do.

But it’s one of the hardest things to do well.

To get your lyric to sound like a simple statement or a conversation that happens to rhyme.

To not show the songwriter behind the song.

That’s hard.

Like… really hard.

It’s easy to hide behind a veil of vague metaphors and cool sounding lines.

And yes, there’s a time and a place for that.

Especially if your music is undeniably great.

But if that’s all you ever do, your songwriting skills will stay stuck in second gear.

Because fog can’t fail.

Clarity can.

Stephen Sondheim said it best with his personal songwriting principles:

Nothing else matters if the listener can’t tell what you’re trying to say.

And if you don’t know what you’re trying to say, that’s even worse.

That said, I never told my friend she was wrong.

Songwriting can be poetry.

Sometimes it should be.

But thinking of lyric as pure poetry gives us permission to hide.

To blend in behind pretty lines instead of doing the hard thing:

Saying what we mean and saying it well.

So next time someone says your lyrics are poetry, see it as a warning sign.

Then sit your ass down and write a simple song.

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This past week I sat down with a song I’ve been rewriting for years.

It’s got this chorus I absolutely love…

But I’ve never been able to get the verses right.

And as Yeats said:

“A line will take us hours maybe;

Yet if it does not seem a moment’s thought,

Our stitching and unstitching has been naught.”

So I do my best not to sit with it for too long.

But it keeps calling me back.

Every few months, I take another swing.

I’ve probably struck out 15 times on this one song over the years.

But the thing about songwriting is you get as many at-bats as you want.

Well today, it finally connected.

After strumming around on my guitar for a bit, I knew I was close.

But I didn’t want to think too hard and overwrite.

So I got up and went for a run.

Came home, made some oatmeal, showered, and sat back down.

Thirty minutes later, the line pretty much fell into my lap.

Now, I know it might not be finished.

I might sit down next week and change that line again.

But I’m at least in the ballpark.

And for a few minutes this morning, I got that feeling.

That feeling where you listen back to your demo and you keep playing it over and over because there’s nothing that jumps out at you.

Nothing feels wrong anymore.

You reached the top of the mountain.

And all you can think is, I can’t believe I made it up here again.

You may even think to yourself, “that wasn’t so hard after all…”

But you don’t care even if it is hard.

You’d do it again and again for this feeling alone.

Not the feeling of writing a song, the feeling of having written a song.

A good song. One that moves you.

And that’s a tall order.

It’s exhilarating and painful at the same time, and only worth it once you’ve reached the top.

That’s when the weight falls off your shoulders.

You didn’t know it was there until it does.

And you can’t believe you’ve made this magical thing that floats through the air and makes you feel stuff.

The best part, you can now share this thing with others and it might even make them feel something too.

That’s a powerful feeling.

And you’ll do anything to feel it again.

It reminds me of the first time I ever made music with my friends.

We were probably twelve or thirteen, playing Free Bird in the upstairs bedroom.

One drum set and two guitars.

We must have stumbled through it twenty times until we finally locked in.

And when we did, we just looked at each other and smiled. Then threw our heads back and howled with laughter.

Nobody had to say anything.

We all felt the magic.

And that’s what I’m chasing with every song, every rewrite, every production.

I’m always trying to get to the top of that mountain.

And the funny thing is, you never remember the climb.

You just know you’re standing there again, out of breath, looking at something you didn’t have the day before.

So you go back down and you find another mountain.

And you start again.

Not because you have to.

Because you know what’s waiting at the top.

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Most artists think they weren’t built to sell.

I’d certainly put myself in that camp.

Promoting my work has always felt like an entirely different skill for me.

Like I’d have to access a different part of my brain to even know how to start.

Analytics, Facebook ads, content hooks…

Just typing that out made my eyes glaze over.

I’ve always told myself that if the song is good enough, it will sell itself.

Don’t they say great work rises to the top?

In some cases, sure.

But it’s best not to set your expectations on being an outlier.

Besides, the greatest artists in history had to sell their work…

Picasso built close relationships with art dealers who put his work in front of the right collectors at the right moment.

David Bowie deliberately reinvented his persona, using each new identity to capture attention and give his music an aura people wanted to dive into.

Charles Dickens toured around giving live readings of his own books, helping him reach more people and build a bigger audience.

All of this is marketing.

These artists didn’t shy away from the business side of things.

They leveraged their creativity to give their work the attention it deserved.

They treated selling as part of the craft, not as something they’d maybe do when they got around to it.

Selling your work takes forethought and planning.

Positioning yourself is a creative act… just like writing a song or painting a sunset.

It’s the same attention to detail directed down a different path.

Instead of illuminating a feeling, you’re illuminating your finished work.

So first off, if you've been avoiding selling yourself because you assume you're not built for it, that belief is worth examining.

At the foundational level, an artist is a professional observer.

You can use that to your advantage.

What makes people pay attention?

How does this thing add value to other people?

What’s the best way to communicate that value?

And communication is key.

That’s why we make songs and books and paintings in the first place.

Selling is simply the final act of communication before the work is actually completed.

So next time you finish your work, try asking this one question:

“Who is this for, and how do I make sure they see it?”

You already know how to answer that question.

You just haven’t been asking it out loud.

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“The music business is a cruel and shallow money trench, a long plastic hallway where thieves and pimps run free, and good men die like dogs. There's also a negative side.“

I love this quote.

Apparently, Hunter S. Thompson first said it about TV and journalism.

But, in a classic game of internet telephone, it got changed to reflect the music business.

And after fourteen years working in this industry, I can’t disagree.

The business of songwriting is rough.

You'll likely spend years working in the darkness before your songs ever get any real recognition.

Fortunately, there’s a way around the heartache and despair that comes from bearing your soul while remaining invisible.

The thing is, you can come at this business from one of two angles:

You can adopt the mindset of a songwriter working in the music business.

Or you can adopt the mindset of the artist.

These sound similar, but they lead down radically different roads.

The music business runs on a clock.

It wants new. Young. Beautiful.

Experience isn’t always an asset. Sometimes it’s a liability.

The more you know, the more you see behind the smoke and mirrors, the more the magic fades.

But the artist…

The artist has no age limit.

Picasso didn’t peak at thirty-three.

Leonard Cohen barely broke ground until his forties. And he kept releasing music into his eighties.

The work deepens because the person deepens.

And the person deepens by doing the work. Not for days, but for decades.

Embracing age gives you a reason to keep going:

• You care less about what others think.

• You become more capable of vulnerability.

• You’ve had more time to get to know yourself.

And people can feel that underneath your words.

People want to sense that you’re a little bruised. Because they are too.

They want to believe you’re not just wearing the mask of wisdom but that you’ve walked the path and you’ve earned it.

You’ve earned it by staying true to your creative calling even when it breaks you.

Because you love the act of creating.

And the truth is, if you’re not doing this for love, you’re doing it for the wrong reason.

With love, the timeline stops being a threat.

I mean, why would you want it to end? Why would you want to peak?

You’re doing what you love every day.

And you’re becoming more and more capable of moving others with your work.

Moving yourself too.

That shallow trench Hunter S. Thompson was talking about, it only kills the ones chasing the clock.

The artist isn’t concerned with these things at all.

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I woke up early last Friday.

Stumbled downstairs, poured some coffee.

Switched on my little red bluetooth speaker.

After a full week of producing demos for other artists, I couldn't wait to listen back to the last song I wrote for myself.

I grabbed my phone and opened my handy dandy voice memo app.

But alas… there was no recording of my recent song.

That’s when I remembered, there was that one line in the bridge I couldn’t quite get last week.

“Hmm, this calls for another cup of coffee,” I thought.

An hour and a half later, I was still mumbling the same nonsense over the bridge melody. Searching for the best five words.

But nothing I was saying felt right.

Luckily I’d been there before.

I knew what my move would be:

Write down exactly what I meant to say, in plain English.

Next, record a quick voice memo and put the song away for another few days.

One listen with fresh ears and I’d know whether the line works (and if the song is even worth keeping).

It might be garbage, it might be gold.

But the truth is I won’t know unless I embrace the uncertainty of not knowing yet.

Which begs the question.

Why is not knowing so hard to sit with?

For me it’s not just songs.

It’s everything that has to do with my art.

The writing, the production, the mix, the content.

I’m always looking for certainty before I make a decision.

Asking people what they think.

Triple checking for clicks and pops in the vocal track.

Before I finish a mix, I send it to my mastering engineer to double check.

Because I need someone else to tell me it’s done.

But he always says the same thing.

Sounds good. Send it.

It’s not like he’s hearing something I’m not.

It’s just that he’s not zoomed in the way I am. Hyper-fixated on the tiny details no one’s ever gonna notice.

That’s what the coffee-and-bridge block that morning was really about.

I wasn’t stuck on the line.

I was looking for a shortcut around the uncertainty and discomfort instead of just living in it for a while.

Fast forward five days and I’m listening back to that voice memo.

And guess what?

I think the song is worth keeping.

And there are definitely lines I’ll need to rewrite. But the one line in the bridge that makes the cut is the one I wrote down in plain English.

The one I wrote down as a placeholder to give the song some time to breathe.

It goes to show we can’t judge our art as we’re making it.

It needs that time tucked in a drawer, so we can see it again with fresh eyes.

And as for uncertainty, that’s price of admission.

Not getting comfortable with the answer.

Getting comfortable with the waiting (as Tom Petty said, that’s the hardest part).

Because that’s what it takes to know for certain.

The uncertainty isn’t in the way of your work.

It’s how your best work gets finished.

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A great piece of music should take you on a journey.

Whether it’s Beethoven’s 3rd or a three minute pop song, when it’s done right, music lets you lose yourself in the moment.

It takes you out of time.

One of the main ways it does this is with dynamics.

A track builds through waves of tension and release until the ecstasy of the final chorus.

Most people think about dynamics as a melody and production thing… a laid-back verse into a sky-scraping chorus.

But to make your song great, your lyrics should build along with your music.

Unfortunately, most songwriters think the opposite.

They think they need to start with their biggest, boldest lines.

Because of course, that has to be the best way to grab the listener’s attention.

But that only confuses the listener, and a confused listener tunes you out.

“You want to be a writer
But you don’t know how or when
Find a quiet place
Use a humble pen”

- Paul Simon

When you open a song with your most poetic lines, you’re asking a lot from the audience right off the bat.

They don’t know enough yet.

You barely have your foot in the door.

They’re still wondering what the song’s about, who’s talking, what’s at stake.

In fact, it’s better for the audience AND your lyric if you wait to unveil your best lines.

When you start small, with a simple image or a conversation, you let the listener identify with the character in your song.

And once they’ve identified with that character, those big lines hit way harder.

Here’s why…

If you’re doing your job right, the listener isn’t just passively enjoying your song.

They’re following your lead and building a world in real time.

That takes mental bandwidth.

Hand them an abstract image in line one and you’re asking them to do two things at once: build the world of the song AND decode a metaphor.

Most people can’t do both, so they default to the easier one.

You need to build your world first.

Let them walk around in it for a verse and a chorus.

Once your world exists, you can shine a spotlight on whatever you want.

Okay great, but how do you actually do this?

You show before you tell.

Start with a tangible for line one.

Just one thing that’s objectively true:

• A broken down car on the side of the road.

• An old love letter you found in your junk drawer.

• A midnight phone call that you know you shouldn’t pick up…

Let your story unfold naturally.

You’re not being simple for the sake of it.

You’re giving the listener something to stand on.

If you keep verse one literal, and focus on your big idea in the chorus, then you’ll have a great foundation for those poetic lines in your second verse and bridge.

You can start interpreting the scene instead of just showing it.

And if you do this right, your chorus will hit harder each time.

That’s what I mean by lyrical dynamics.

What you say in your second verse and bridge will show your chorus lyric in a whole new light.

Save your best, most poetic lines for the second half of your song.

Let each chorus become bigger than the previous.

When it’s done right, it feels like magic.

And all the listener knows is you just made them lose track of time.

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I was meditating the other morning,

giving the French press some extra time to brew…

When it hit me.

I might never get what I set out for.

I might never write chart topping hits or have a massive impact on the music industry.

And I’m okay with that.

Not because I feel like I’ve done enough.

Sure, I’ve had songs on the radio. I have over 100 million streams as a writer/producer. My music has been placed in film and TV. I’ve even had songs chart overseas.

Those are all things I wanted.

But that’s not all I set out to do.

Eight years ago, I had bigger dreams.

I moved from New Jersey to LA chasing them. Finally ending up in Nashville.

When it comes to music, a part of me has always been attached to an outcome.

That big song that changes your life forever.

Sitting there, breathing, I realized I may never get that.

But I don’t need it.

That’s the thought that surprised me.

I’ve been holding on to the possibility for so long.

Every session, every co-write, every song I’ve put out under my own name, every cut I’ve had for someone else…

I was always betting on the big one.

The one that gets you into rooms with the biggest artists and producers in the world.

I never imagined a future where I wouldn’t eventually achieve that dream.

Now, I’m not saying wanting that is wrong.

Wanting more is what drives you to keep working after years of disappointment.

But somewhere along the way, that wanting turned into needing.

And to need something makes you a slave to that thing.

You can want something and still be free. Needing something is a different story.

I can’t make a hit happen.

I can’t make a song go viral.

Those things were never mine to control.

But what can I do?

• I can write the best song I’m capable of writing.

• I can say yes to an opportunity that might move the needle.

• I can show up every morning and lay my pen at the feet of the muse.

Those things are mine to control.

And the only real choice I have is what I do with them.

I think about how I once pushed myself to write a song a day for 100 days.

By day 97 I was completely spent.

There was no part of me that wanted to write a song.

So I set a timer for twenty minutes and tried something I never thought would work.

Before I knew it, time disappeared. Timer be damned.

One hour later I’d written one of my favorite songs up to that point.

That's what surrender looks like in practice.

It’s not giving up, but continuing to work without needing to know how it ends.

If I’m doing the work I’m meant to be doing, there’s nothing else I need.

The hits, the impact, the Grammys and the gold records…

those things would all be swell.

But they’re not the prize.

The prize is getting to sit down with my guitar and a cup of black coffee before the sun comes up and try once more to turn air into magic.

It's a co-write with a total stranger that turns into a decade-long friendship.

It's a couple I've never met asking me to play my song for their first dance.

Those are the moments that make all of this mean something.

So when I say I’m okay if the big one never comes, I don’t mean I’m okay with losing.

I mean there was never anything to lose in the first place.

And just like that… 20 minutes was up.

Meditation over, I opened my eyes.

Got up from the couch and poured my coffee.

Same living room. Same stack of books on the coffee table.

Nothing had changed.

Except now I knew something I didn’t know 20 minutes before.

I might never get what I set out for.

And that’s fine.

Because I already got what I came for.

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Sunday morning 3am.

Body tired, mind… wired.

I was thinking in circles.

Everything I hadn’t done.

• Songs unfinished.

• Emails unanswered.

• Production demos and deadlines.

• The next release, the one after that.

Two hours later my brain finally gave up and let me sleep.

Next thing I knew it was 7:15.

I stumbled to the French press and grabbed my journal.

Wrote down everything that was weighing on me.

My brain must have been working overtime while I was asleep, because the answers just came.

And underneath it all was the same overlooked fact.

I get to work with music.

Every day, with people I respect, I get to do the thing I was made to do.

Somewhere under the obligations and the deadlines I’d stopped seeing that as a gift and started seeing it as a job. As something I owed people.

But I was given something.

A deep love for music and words.

An ability to turn emotion into sound.

Something I’d been developing for years.

That’s a gift.

And you don’t say thank you for a gift by keeping score of what it gives you.

You say thank you by giving it away.

I’m done treating this like a race.

Not because the urgency isn’t there.

The world doesn’t stop spinning…

That’s why I’ve released a song every four to six weeks for almost two years straight.

But right now, if I keep that pace, I know what happens next.

I start forcing songs out before they're ready, just to hit a deadline I set for myself.

And a gift forced out the door isn’t much of a gift.

There’s always enough time.

Enough time to make my music.

Enough time to help others finish theirs.

If it feeds you, it’s a gift.

And the only way to say thank you for a gift is to give it away completely.

No scorecard.

No performance for anyone watching.

Just, “here you go.”

This is what I was given.

I’m giving it back.

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It’s been almost two years since I started sharing my own songs again.

From fall 2024 to summer 2026, I’ve released a new single every four to six weeks.

I told myself I’d do this for at least two years… figuring that would be enough time to find a few fans and trigger some sweet Spotify algo magic.

As of right now, I’m prepping releases to close out the two years.

But to be honest, I’m losing steam.

I’m not sure I even like the song I’m currently working on.

Not because it’s bad. I know it’s not.

It might be better than anything I’ve put out in months.

But that’s the thing, I have no clue.

I’m too focused on getting it out the door to feel anything.

Something in me wants to slow down.

Something else is scared that if I do, I’ll lose whatever I’ve built.

Why the four to six week deadline?

That’s the cadence they tell you to follow to stay visible and feed the algorithm in your favor.

So I wrote the songs, marked my calendar, and committed.

For almost two years, I’ve kept that promise.

But at some point the deadline stopped serving the songs and started running the show.

Instead of asking myself: “is this the best I can do.”

I’ve found myself asking: “is this done enough to hit the date.”

And those two questions produce drastically different works of art.

I’m not saying I want to stop.

I’m not saying the last two years are anything I wouldn’t do again.

I’m proud of the work I’ve done so far.

But I want to keep it that way.

And I can feel the difference between a song I finished because it was ready and a song I finished because the calendar said so.

I believe the audience can feel that too.

But there’s something else.

I’m a songwriter.

Sure, I’m also a producer. I get hired for it and I’m good at it.

I’ve been writing and producing for the same number of years.

But if you asked me which one I am beneath the surface, it’s songwriter.

And these past two years, I haven’t been immersed in the writing the way I used to be.

I used to:

• Read about songwriting every morning.

• Listen to songwriting podcasts at the gym.

• Finish songs in the shower before my day even got started…

But somewhere in between all the releases, that fell away.

I stopped giving the writing room to breathe.

I started treating the release calendar as the thing that proves I’m serious.

But I haven’t felt this off my game in years.

So I’m making a deal with myself.

I’m going to slow down the releases when I need to.

Give the songs room to be finished because they’re ready, not because a date on the calendar says so.

Take that time to get back to the writing itself.

But the other end of the bargain is this:

I have to start promoting the songs that are already out on a more consistent basis.

Because that’s one part of the path I haven’t fully explored.

I’ve got songs in the pipeline I really care about.

I don’t want to rush their production just to hit a deadline.

I’d rather give them the time they need instead of just shooting them off into some four-to-six-week churn.

So I need to learn to promote my work.

Getting comfortable with that now means I'll know exactly what to do with the songs once they're ready.

Two years is nothing in the span of a life spent making music.

I’m not doing this for a season.

I’m an artist, and I plan on being one until the day I die.

For six years before this, I sat on the sidelines:

• producing for other people

• promoting other people’s voices

• keeping my own songs on the hard drive.

Simply getting back on the field is something I’m proud of.

But if I’m going to be out here for the rest of my life, there’s no reason not to slow down long enough to make sure I’m doing it right.

I’m not stopping.

And I’m not afraid of showing up too late.

A four-to-six-week deadline was never what proved I was serious.

What proves I’m serious is years and years of releasing music, no matter what the timeline looks like.

There’s always room for better.

I’ve got time to take it.

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I didn’t write a single word for the past two weeks.

• No lyrics.

• No newsletter.

• Not even a throwaway note in my phone.

I was visiting friends and family, half-working on making demos, mostly just being present with people I care about.

And somewhere along the coast of New England, it stopped.

That constant buzzing in the back of my mind.

It just stopped.

I looked up and saw the replay of my life over the past year.

• Write a song.

• Race to finish the production.

• Send it out to the world, post about it once or twice.

• Then hurry up because it’s almost time to release the next one.

All while writing this newsletter, keeping up with content, session work, building a business…

I hadn’t stepped back once to see what was working and what wasn’t.

Ten days off didn’t just reset me,

It let me see my life through fresh eyes.

I could finally stop working for my goals and start working on my goals.

Sorting through everything I’d been too busy to face head on:

• What actually lit me up.

• What I’d been doing just because of convention.

• What things will actually make me fulfilled in the long run.

You have to make room for clarity like that.

The subconscious doesn’t clock in when you tell it to.

It works in the background, on its own schedule, when you’ve stopped interrupting it with made-up deadlines.

I didn’t come back from this trip with a new song.

I came back with something better:

A clearer sense of what’s worth making, for me.

I’d been treating consistency as the whole game.

• Show up every day.

• Share a song every six weeks.

• Keep the machine running at all costs.

But creative work is more like tending a garden than building a machine.

You don’t force it into existence.

• You show up,

• You water it, pull a few weeds.

• You trust what you can’t yet see.

Then one day you look up and you’re standing in the middle of a field of wildflowers beside the highway…

Now don’t get me wrong, showing up matters.

And I’m gonna keep doing it.

But somewhere along the way, “showing up” turned into “producing at all costs.”

Those aren’t the same thing.

I was so close to the work that I couldn’t see it clearly.

Stepping back gave me space.

And that space gave me perspective.

I could finally see the world I’d been building instead of just the next thing on the horizon.

I could ask a bigger question than, “what’s the next thing?”

I could ask how this next thing helps to build the story of my life.

The story I want to tell by the end of it.

None of that is visible with your face pressed up against the glass.

You have to step back if you want to see the whole path.

Rest isn’t a break from your work. It’s part of it.

But how many of us actually put this into practice before the work makes us take a break?

You don’t have to earn rest by burning out first.

You can choose it on purpose, before the grind grinds you down.

And when you do, don’t just wait to feel refreshed…

Pay attention to what surfaces when the dust settles.

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Still on the road this week, seeing family and friends. Topped off the trip seeing Paul Simon at Forest Hills Stadium in Queens.

Watching him, I was reminded about creative constraints. Which prompted me to dig this one out of the vault — one of the first newsletters I ever wrote.

I couldn’t help but laugh when I realized it includes a line from Paul Simon himself about writing “backwards.” Made me want to reshare it.

Here are three creative constraints for writing songs faster.

In a world where artists are expected to create nonstop, speed is a superpower.

When I started my songwriting journey it would take me weeks to finish one song.

Now I can write one between breakfast and lunch (and still have time for a pre-lunch work out).

I do this by embracing creative constraints.

Unfortunately, most writers waste years writing songs without ever setting constraints for themselves.

Why?

They don’t understand the power of limitation.

Creative constraints are boundaries you set for yourself. They help you get more work done by giving you less to work with.

The greatest writers of all time did this.

Robert Frost likened writing free verse (poetry without a regular meter) to playing tennis without a net.

You might think this would crush your creative spark.

But constraints actually make you more creative.

Because when you limit your options, you’re forced to stretch yourself to come up with something unique. Something that fits within the guidelines you’ve set.

Not only that… you get to choose the constraints you work with.

You can even invent your own.

In this newsletter, I’d like to share three of the most helpful constraints I’ve found so you can use them to write more songs in less time.

Here are 3 time tested creative constraints to help you do that.

Perfect Rhyme

Rhymes are considered “perfect” when they end with matching vowel and consonant sounds, like smash and crash.

“Imperfect” or “slant” rhymes have matching vowel sounds with different consonants at the end, like smash and craft.

Perfect rhyme helps you write fast by giving you fewer options to work with.

The one trick to using perfect rhyme:

Avoid clichés like a cat avoids a bath (which pretty much rules out the word love).

Are you starting to see how this can boost creativity?

Using perfect rhyme makes you stretch to find new and better words.

Try it for yourself:

Write your next song using 80% perfect rhyme.

Notice how the perfect rhyme feels in comparison to the imperfect rhyme.

Start With The Title

Starting a song without a title is like driving around town on an empty stomach looking for something to eat.

Bad decisions at every turn.

When you start with a title, you know where you’re going.

Now all you have to do is let the lyrics lead you there.

You can even write backwards from the title. As Paul Simon says:

Whatever way you choose, this makes your songs more clear.

And when your songs are more clear, they have a better chance of connecting with your audience.

Writing more songs in less time AND building a better connection with your audience...

These constraints are starting to look pretty good.

Structure Each Section’s Melody Using AABA

This one took me years to learn.

We know about song form. But great songwriters go deeper.

They see the hidden structure inside every section.

The chorus melody has a structure. So does the verse melody.

The most efficient one I’ve found is AABA:

• Do something once

• Now repeat that thing

• Now do something different

• Now go back to the first thing one last time

This is a quick way to create a feeling of completion for the listener.

It also eliminates the question, “do we need a pre chorus?”

No, we don’t.

The song feels great just like this:

• Verse 1 - AABA

• Chorus 1 - AABA

• Verse 2 - AABA

• Chorus 2 - AABA

• Break (repeat the title and/or ad-lib melodies over the same chords).

• Chorus 3 - AABA

Assuming your chorus doesn’t change, this lets you write a 12 line song.

Now the only question is, how long does it take you to write 12 lines?

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I’ve been on the road this week, no time to write something new.

So instead of forcing it, I’m resurfacing one of my favorite essays: Sondheim’s four rules for songwriting.

Still worth the read, even if you caught it the first time.

Stephen Sondheim didn’t just write lyrics, he built worlds out of words.

His musicals stretched the limits of what songs could do.

Every line was precise, deliberate, and alive with clarity.

In Finishing the Hat, his book on the craft, he shared his four deceptively simple principles for songwriting:

• Content dictates form

• Less is more

• God is in the details

• All in the service of clarity (without which nothing else matters)

Taken together, these principles reveal why his work feels both surprising and inevitable.

Let’s break them down and see how they can sharpen your own songs.

Content Dictates Form (Start With the Emotion)

What you’re saying determines how you say it.

In other words: start with the emotion, then shape the form around it.

Let the lyric’s feeling decide the pacing, rhyme scheme, and melody.

This is how artists like Radiohead or Paul Simon write songs that feel unrestrained yet natural.

They don’t force their ideas into preset molds. The content bends the form.

Another songwriter who did this naturally was John Lennon.

When he had a lyric that lasted longer than the measure of music he was writing, he simply added a measure or two.

The content is what you have to say.

The form is simply the packaging you put it in.

Try this: Instead of squeezing your words into the music, let the music expand to hold your words.

Less Is More (Say Less, Mean More)

Every songwriter knows the game:

So much to say, and only three minutes to say it.

The solution?

Always say less than necessary.

Sondheim believed in giving the audience just the primary colors, trusting them to paint the rest.

Suggestion is often stronger than explanation.

Don’t try to say it all.

Let the audience fill in the details with their own lives.

This makes the song more personal to them.

And when the song is more personal to your audience, you win.

Think of a line like Paul Simon’s:

“Hello darkness, my old friend.”

Four simple words. Behind them lies a history of heartache.

Try this: Cut every unnecessary word from your lyric. Feel the weight lift.

God Is in the Details (Make it Sound Specific)

The specific is the universal.

Listeners will always paint their own picture.

But if you feed them only vague words, that picture will be pale and lifeless.

You have to be willing to get dirty.

Dig with your hands. Show us the dirt under your fingernails.

Details make a song more believable.

Try this: Swap a vague word or two for a concrete image. Feel your lyric come alive.

All in the Service of Clarity (Cut Through the Noise)

Every road leads here.

A song is one moment, one primary feeling, captured in sound.

If the listener can’t tell what you mean, nothing else matters.

• The clever rhyme won’t save you.

• The dazzling imagery won’t save you.

• The unexpected chord change won’t save you.

Clarity is what moves people.

And here’s the main takeaway:

When you focus on clarity, the other principles fall into place.

The content shapes the form. The words get leaner. The details sharpen.

Clarity isn’t about dumbing it down.

It’s about cutting through the noise so the heart of the song sings out.

Sondheim’s rules remind us that songwriting is a fine art because they balance imagination with discipline.

The daring comes from honoring the truth of your content.

The transformation comes from shaping it clearly enough to move someone else.

And remember:

Clarity moves people. Everything else serves that.

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For six years, the only songs I shared were sung by someone else.

Co-written, mostly. For other artists to sing.

Nothing went out under my own name.

I told myself that was okay.

I was burned out on chasing attention. Tired of playing shows, putting myself out there, feeling vulnerable…

Anyway, my songs were reaching more people than I ever had on my own.

Wasn’t that the point?

But there were nights I’d lie awake and feel this burning in the pit of my stomach.

I’d stare at the ceiling wondering why I gave up on myself.

How I was giving in to fear.

Counting the time I had squandered by not sharing my own songs.

I love writing for other artists. I still do. Being a creative behind the song is its own kind of dream, and I’m not done chasing it.

That was never the problem.

The problem was that I let it become the only thing. I poured everything into other people’s records because somewhere along the way I’d decided my own voice wasn’t good enough to carry one. Not as good as the artists I was writing for. Not “pop” enough to be relevant.

So I told myself the behind-the-scenes work was the whole dream. That way I never had to risk the rest of me.

But it wasn’t a strategy. It was fear wearing a more practical coat.

So I dealt with the occasional dark night of the soul…

Until that feeling went away.

That’s when I started to really worry.

Had I ignored my dream so long that it stopped calling?

It sounds ridiculous, because I’m sure that’s the part where most people shrug it off and let it go. But I couldn’t do that.

So I started releasing my own songs.

Not as some grand reinvention.

Just one song, then another.

Putting them out under my own name again.

And to my surprise, they performed pretty well. Way better than I expected.

Which brought a fear I didn’t see coming: now I had to follow each song with something just as good, or better.

That pressure hasn’t let up.

I’m releasing on a schedule I set for myself, and half the time I’m scrambling to get the next song finished before my own deadline.

And each time, some part of me is still afraid that I won’t be able to do it again.

But here’s what I didn’t expect.

Releasing my own work didn’t cost me the other work. It fed it.

The more I write for myself, the better I am in the room with everyone else.

The two were never competing for the same space in my life. I’d just convinced myself they were so I’d have a reason to skip the scarier one.

I still take the sessions. I still want the cuts.

None of that changed.

What changed is that I stopped waiting for permission to also be the artist.

I stopped chasing the version of the industry where you grind and angle and hope someone hands you the golden ticket.

I just started sharing the work — the songs, this newsletter — and letting the opportunities find me instead of the other way around.

Because no one is making me do this.

There’s no label waiting on the next song. No deadline anyone handed me.

The schedule I’m scrambling against is one I invented. I could stop tomorrow and the only person who’d notice is me.

For years, that was exactly the loophole.

No one was asking me to be an artist, so I never had to be one. I could pour myself into other people’s records and call the rest of it impractical.

The absence of pressure was my permission to never try.

Now I’m the one applying the pressure.

And the rush I feel to finish the next song is the whole thing turned right side up.

You don’t scramble to follow up work you don’t care about. The deadline only exists because I’m finally doing the work I always wanted to do.

I'm not behind the scenes anymore. I'm not in front of them either.

I'm just in it.

I used to lie awake afraid the dream had gone quiet. Now it won’t shut up. I’ll take it.

You don’t have to quit the thing that’s working to start the thing that’s yours.

You just have to stop using one as the excuse to never risk the other.

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Most days I write whether I feel like it or not.

Not because I’m disciplined.

Because I figured out a long time ago what happens when I don’t.

I go a few days without writing and I feel restless. Like something in my life is off balance and I can’t say what.

When I start writing again it goes away.

Everything feels okay.

That’s why I can’t call it discipline.

Because you don’t need discipline to eat or sleep or breathe.

We treat making things like a luxury.

Something you earn after the real work is done.

But I think that’s backwards.

Making things isn’t the reward for a working life.

It’s part of what keeps your life working.

Food and sleep keep the body alive.

This keeps the rest of you alive.

But there’s a second part to this, and it’s the part most people skip.

That part is sharing your work.

When you share something true, you’re saying: this is what life feels like for me.

And every so often, someone says it back.

“Me too.”

That me too does something the work alone can’t do.

It reminds us we’re not the only one.

The work does its job the moment you make it and let it out.

Everything after that is a different conversation.

The likes, the streams, the views…

They measure how far it traveled.

Not whether it worked.

A song can do its job for you and still only get nine plays.

The trap is letting the numbers become the point.

Because the moment they do, you start writing for the numbers and not for you.

And the thing that was keeping you sane turns into another job you’re trying to win.

I’ve done that.

We all do that…

But it’s a bad trade.

You hand over the one thing that was yours for a metric anyone can move.

So I try and keep the two separate.

What the work does for me and whether I share it, I get to keep.

What it does in public was never mine to begin with.

So make your thing.

Whatever it is.

Not because the world is asking for it.

Make it because of what happens if you don’t.

Let it reach whoever it reaches.

One person is enough.

One person is the whole point.

And when the numbers come, or don’t, remember they were never the reason.

You didn’t make it to be counted.

You made it to feel like yourself again.

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